Granted Patent B2

US 12,673,962 · App. 17/823,631 · Granted Jul 7, 2026

Inventors: Peter Wolohan (Princeton Junction, NJ); Tyler Fleetham (Yardley, PA); Hsiao-Fan Chen (Lawrence Township, NJ); Fadi M. Jradi (Abington, PA)

Assignee: Universal Display Corporation

C07F5/027H10K50/11H10K50/16H10K85/30H10K85/658

Abstract

Claims (51)

1 . An organic light emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode,

wherein the organic layer comprises a compound having a structure of Formula I:

wherein

rings A, B, C, D, E, and F are each independently a single or fused ring system, consisting of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;

L 1 , L 2 , L 3 , L 4 , L 5 , and L 6 are each independently optionally present or is selected from the group consisting of O, S, Se, BR, BRR′, NR, C═R, CRR′, SiRR′, P(O)R, and GeRR′;

a, b, c, d, e and f are each 0 for not present or 1 for present;

a+b+c and d+e+f are each greater than or equal to 2;

with the proviso that the following two conditions are true:

1) when a and d are both 0, then rings A and D are not both benzene rings linked through a C—C bond para to the two boron centers, and

2) when rings A, B, C, D, E, and F are all benzene rings and a and d are both 0, then L 2 , L 3 , L 5 and L 6 are not all NR;

R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;

each of R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;

any two of adjacent R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 can be joined or fused to form a ring; and

the organic layer is an ETL.

2 . The OLED of claim 1 , wherein the ETL further comprises a second material.

3 . The OLED of claim 2 , wherein the second material is a metal or a metal complex contains at least one selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, a post-transition metal, and an organic complex of a rare earth metal.

4 . The OLED of claim 3 , wherein the metal complex contains Li, Al, Yb, Sm and Ca.

5 . The OLED of claim 2 , wherein a work function of the second material is ≤4.5 eV.

6 . The OLED of claim 2 , wherein the percentage of the second material is at least 1%, 5%, 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 95%, 99%.

7 . The OLED of claim 1 , wherein the compound of Formula I has an electron reorganization energy that is ≤0.5.

8 . The OLED of claim 1 , wherein the OLED further comprises an EML disposed between the anode and the cathode.

9 . The OLED of claim 1 , wherein the compound having the structure of Formula I is deuterated or partially deuterated.

10 . The OLED of claim 8 , wherein the ETL and the EML are the same type of material.

11 . The OLED of claim 8 , wherein the ETL and the EML are exactly the same material.

12 . The OLED of claim 8 , wherein the EML further comprises a first host.

13 . The OLED of claim 8 , wherein the EML further comprises a second host.

14 . The OLED of claim 8 , wherein the EML further comprises a third host.

15 . The OLED of claim 8 , wherein the compound of Formula I is at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated.

16 . The OLED of claim 12 , wherein the first host is at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated.

17 . The OLED of claim 13 , wherein the second host is at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated.

18 . The OLED of claim 14 , wherein the third host is at least 30% deuterated, at least 40% deuterated, at least 50% deuterated, at least 60% deuterated, at least 70% deuterated, at least 80% deuterated, at least 90% deuterated, at least 95% deuterated, at least 99% deuterated, or 100% deuterated.

19 . A consumer product comprising an organic light-emitting device (OLED) comprising:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode,

wherein the organic layer comprises a compound having a structure of Formula I:

wherein

rings A, B, C, D, E, and F are each independently a single or fused ring system, consisting of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;

L 1 , L 2 , L 3 , L 4 , L 5 , and L 6 are each independently optionally present or is selected from the group consisting of O, S, Se, BR, BRR′, NR, C═R, CRR′, SiRR′, P(O)R, and GeRR′;

a, b, c, d, e and f are each 0 for not present or 1 for present;

a+b+c and d+e+f are each greater than or equal to 2;

with the proviso that the following two conditions are true:

1) when a and d are both 0, then rings A and D are not both benzene rings linked through a C—C bond para to the two boron centers, and

2) when rings A, B, C, D, E, and F are all benzene rings and a and d are both 0, then L 2 , L 3 , L 5 and L 6 are not all NR;

R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently represent zero, mono, or up to a maximum allowed substitution to its associated ring;

each of R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; and

any two of adjacent R, R′, R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 can be joined or fused to form a ring; and

wherein the organic layer is an ETL.

Assignments (1)

Continuity (3)

References Cited (400)